Sounds awesome. Sounds a little like the gym I do my event training in. There is a "public" portion for the MMA guys, but the strongman stuff is in a big warehouse behind the gym, and only a couple people have keys to get in.

Some of your difficulty in breaking the tracks might be the shoes (to quote Spike Lee). When I pull/drag I have to wear shoes with a pretty agressive tread on it, I can't pull for crap in my chucks, too slick. Same thing for tire flipping. For carrys I'm much better in my chucks. I know a lot of guys even pull/drag in rock climbing shoes.

250lbs, large surface area or no would be a real pain to pull. That sounds awesome! Do they have a harness for it?

Feeling up to some of the other implements now?